Synthesis
General procedure for the synthesis of 7-amino-1-tetrahydronaphthalenone from 7-nitro-3,4-dihydro-2H-1-naphthalenone: (i) To a methanol (50 mL) solution of 7-nitro-1-tetrahydronaphthalenone (1.95 g; 10 mmol) was added sequentially ammonium formate (2 g), 5% Pd/C (1 g) and formic acid (0.5 g; as a catalyst). The reaction mixture was stirred for 30 min. After completion of the reaction, the reaction solution was filtered and the filtrate was concentrated. The residue was extracted with dichloromethane (50 mL + 25 mL), filtered and concentrated the combined organic phases. The product 7-amino-1-tetralone 1.4 g (88% yield) was obtained.1H-NMR (500 MHz; CDCl3): δ 7.32 (d, 1H); 7.03 (d, 1H); 6.83 (dd, 1H); 3.70 (b, 2H); 2.85 (t, 2H); 2.61 (t, 2H); 2.10 (m, 2H).
References
[1] Justus Liebigs Annalen der Chemie, 1927, vol. 451, p. 53
[2] Justus Liebigs Annalen der Chemie, 1955, vol. 596, p. 1,220
[3] Collection of Czechoslovak Chemical Communications, 1933, vol. 5, p. 170,177
[4] Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 13, p. 3574 - 3577
[5] Patent: US2004/167128, 2004, A1. Location in patent: Page 59
